methyl 4-(2-methoxyphenyl)-4-oxobut-2-ynoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(2-methoxyphenyl)-4-oxobut-2-ynoate
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: MCGITOQTCIWHBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-methoxyphenyl)-4-oxobut-2-ynoate 、 2,3-二甲基-1,3-丁二烯 在 zinc(II) iodide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.5h， 以82%的产率得到methyl 2-(2-methoxybenzoyl)-4,5-dimethylbenzoate
  参考文献：
  名称：

  Synthesis of Fluorenone and Anthraquinone Derivatives from Aryl- and Aroyl-Substituted Propiolates

  摘要：

  Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Die Is Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.

  DOI：

  10.1021/ol4023276
• 作为产物：
  描述：

  methyl 4-hydroxy-4-(2-methoxyphenyl)but-2-ynoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 生成 methyl 4-(2-methoxyphenyl)-4-oxobut-2-ynoate
  参考文献：
  名称：

  Synthesis of Fluorenone and Anthraquinone Derivatives from Aryl- and Aroyl-Substituted Propiolates

  摘要：

  Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Die Is Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.

  DOI：

  10.1021/ol4023276

文献信息

• B(C₆F₅)₃-Catalyzed [4 + 2] Cyclization Strategy: Synthesis and Photophysical Properties of 5<i>H</i>-Naphtho[2,3-<i>c</i>]carbazole-8,13-dione Derivatives
  作者：Hong Xu、Bei Wang、Fu-Yu Li、Ji-Yu Wang

  DOI：10.1021/acs.joc.2c02064

  日期：2023.3.3

  compounds under different reduction conditions. The results of photophysical characterization showed that the structure of carbazole-fused derivatives had a significant impact on the fluorescence properties.

  本文通过B(C 6 F 5 ) 3催化的[4 + 2]环化反应，高效地合成了一系列新型咔唑醌类化合物。该方案不仅操作简单、底物范围广、原子经济性高，而且催化剂负载量低，避免使用金属催化剂。此外，我们在不同的还原条件下构建了多种新型咔唑稠合化合物。光物理表征结果表明，咔唑稠合衍生物的结构对其荧光性质有显着影响。
• PROCESS FOR PRODUCING LIGNAN COMPOUND
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0646570A1

  公开（公告）日：1995-04-05

  A process for regioselectively producing a lignan compound of general formula (I) by reacting a lactone compound of general formula (II) with a compound of the formula: R⁷Cl (R⁷ being a tri(lower alkyl)silyl group) in the presence of a base, effecting the addition reaction of an acetylene compound of general formula (III) with the resultant compound, and reducing the product. In said formulas R¹ represents alkyl, cycloalkyl, cycloalkyl-lower alkyl, aralkyl, etc.: R² and R³ each represent lower alkoxy, etc.; R⁴ represents lower alkoxy or hydrogen; and R⁵ and R⁶ each represent lower alkyl.

  一种通过通式(II)的内酯化合物与通式为R⁷Cl（R⁷为三（低级烷基）硅烷基）在碱存在下反应，使通式（III）的炔化合物与生成的化合物发生加成反应，并还原产物。在所述通式中，R¹代表烷基、环烷基、环烷基-低级烷基、芳基等：R²和R³各自代表低级烷氧基等；R⁴代表低级烷氧基或氢；R⁵和R⁶各自代表低级烷基。
• US5488134A
  申请人：——

  公开号：US5488134A

  公开（公告）日：1996-01-30
• CN115594627
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of Fluorenone and Anthraquinone Derivatives from Aryl- and Aroyl-Substituted Propiolates
  作者：Florian Pünner、Justin Schieven、Gerhard Hilt

  DOI：10.1021/ol4023276

  日期：2013.9.20

  Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Die Is Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.